private,
From the beginning: I believe you can save yourself some grief if you get the original color copy to good quality first, then do the conversion to b/w, monotone, whichever. The pink/orange so often seen in photos can look strange in b/w, so I layer some negative masks and adjust color until it smooths as much as possible. I masked some bright distractions away in the background before doing the black and white:
Now when I desaturate, there's almost nothing else to do, some slight light/dark adjustment, a dark vignette to hide some clutter. No face smoothing involved. I didn't crop or anything else so you could compare to your original, and yes I do like it, color and b/w. Very flattering to a young person to have a good relaxed portrait taken.
See skin:
http://farm4.static.flickr.com/3102/...64336006_b.jpg